New pyridine and pyrimidine substituted triazine UV absorbers

ABSTRACT

A compound of formulawherein V, W, X and Y represent N or CH, at least one of V, W, X and Y being N and at least two of V, W, X and Y being CH; andR1, R2 and R3 are each independently of the other hydrogen, C1-C8alkyl, C1-C8alkoxy, nitro, cyano, trifluoromethyl, halogen or hydroxy;with the proviso that the compounds of formulaeare excluded,provides good lightfastness properties to textile fibre materials, in particular PES fibre materials.

The present invention relates to UV absorbing agents (UVA) derived fromhydroxyphenyl-s-triazines, a process for their preparation and their usefor the photochemical stabilisation of dyed or undyed textile materials.

The disperse dyes applied in the dyeing or printing of textile fibrematerials, especially synthetic textile fibre materials, are in somecases substantially damaged when subject to the action of light,especially when simultaneously subject to the action of heat. In orderto avoid such damage, UV absorbers (UVAs) are added to the dyeingliquors and printing pastes when dyeing fibres used in the automotive orswimwear sectors or in so-called “outdoor” articles.

EP-A 0 468 921 describes aqueous dispersions comprising ahydroxyphenyl-s-triazine as UVA, which are suitable as light stabilisersfor textile fibres and which are distinguished by good transport andstorage stability.

However, the ambitious requirements especially made by the automotiveindustry are not met to the full extent by the known triazine UVAs.

It has now been found that the application of triazine-based UVAscontaining heteroaromatic substituents provides for excellent lightfastness and hot light fastness properties.

The present invention relates to a compound of formula

wherein V, W, X and Y represent N or CH, at least one of V, W, X and Ybeing N and at least two of V, W, X and Y being CH; and

R₁, R₂ and R₃ are each independently of the other hydrogen, C₁-C₈alkyl,C₁-C₈alkoxy, nitro, cyano, trifluoromethyl, halogen or hydroxy;

with the proviso that the compounds of formulae

are excluded.

Alkyl and alkoxy groups as the radical R₁, R₂ or R₃ may be linear orbranched.

Examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, tert-butyl, isobutyl, n-pentyl, neopentyl, n-hexyl,2-ethylhexyl, n-octyl and isooctyl.

Suitable alkoxy groups are, for example, methoxy, ethoxy, n-propoxy,isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, isobutoxy, n-pentyloxy,neopentyloxy, n-hexyloxy, 2-ethylhexyloxy, n-octyloxy and isooctyloxy.

Halogen is, for example, fluorine, bromine or, preferably, chlorine.

Preference is given to a compound of formula (1) as defined abovewherein X is N and V, W and Y are CH.

Further preference is given to a compound of formula (1) as definedabove wherein Y is N and V, W and X are CH.

Further preferred compounds of formula (1) as defined above are thosewherein V is N and W, X and Yare CH.

Further preference is given to a compound of formula (1) as definedabove wherein X and W denote N and V and Y are CH.

R₁ in formula (1) is preferably hydrogen or methoxy.

R₂ in formula (1) is preferably hydrogen or hydroxy.

R₃ formula (1) is preferably hydrogen or methoxy.

The compounds of formula (1) can be prepared according to known methods,for instance by the process described in Helv. Chim. Acta 55, 1566(1972).

Accordingly, the invention further relates to a process for thepreparation of a compound of formula (1) as defined above, whichcomprises

(I). to prepare the 2-aryl-4H-1,3-benzoxazin-4-one (4) by acid-catalysedring closure reaction of the salicylamide derivative (2) with thecarboxylic acid (3),

-   -   and

(II). to react the thus obtained 2-aryl-4H-1,3-benzoxazin-4-one (4) withthe amidine (5) to provide the triazine derivative of formula (1),

-   -   wherein R₁, R₂, R₃, X, Y, V and W are as defined above.

The compound of formula (1) is preferably applied in an amount of0.01-15.0% by weight, more preferably 0.1-10.0% by weight and inparticular 0.5-7.0% by weight, based on the weight of the fibrematerial.

The novel UVAs are especially suitable for the photochemicalstabilisation of undyed, dyed or printed textile fibre materials, whichis also provided by the present invention.

A corresponding process comprises treating the textile fibre materialswith a liquor containing at least one compound of the above formula (1).

Textile fibre materials suitable for the treatment are primarily fibrematerials containing polyester or cellulose acetate. The term polyesterfibres should be understood as referring, for example, to celluloseester fibres, such as secondary cellulose acetate fibres and triacetatefibres, and especially linear polyester fibres which may have beenacid-modified, such fibres being obtained, for example, by condensationof terephthalic acid with ethylene glycol or of isophthalic acid orterephthalic acid with 1,4-bis(hydroxymethyl)cyclohexane, and alsofibres of copolymers of terephthalic acid and isophthalic acid withethylene glycol. Customary polyester fibres in the textile fibreindustry consist, in particular, of terephthalic acid and ethyleneglycol.

The textile fibre material to be treated may also be a blend fabric ofpolyester fibres and other fibres, examples being blends ofpolyacrylonitrile/polyester, polyamide/polyester, polyester/cotton,polyester/viscose, or polyester/wool fibres, which are printed or dyedin a customary batch or continuous procedure.

The process according to the invention is particularly suitable for thestabilisation of polyester fibres or blend fabrics of polyester fibresand other fibres, like PAN/PES, PA/PES, PES/CO and PES/WO.

The fibres can be applied in the process according to the invention inany conventional form, for example in the form of microfibers.

Accordingly, the invention further relates to a process for thestabilisation of textile fibre material, wherein the textile fibrematerial comprises polyester fibres.

The novel UVAs are sparingly soluble in water and are therefore appliedin dispersed form. For this purpose, they are ground to particle sizesof ca. 0.1-3.0 μm in accordance with the application conditions using,for example, an appropriate dispersant and with the aid of, for example,quartz beads and a high-speed stirrer.

The application of the UVAs according to the invention can be carriedout prior to, during or after the dyeing process of the textilematerial.

Preferably the UVA is applied simultaneously with the dyes, i.e. it isadded to the dyeing liquor in the exhaust or padding process.

Accordingly, the invention relates to a process for the photochemicalstabilisation of dyed textile fibre material, wherein the compound offormula (1) is applied as a part of the dyeing liquor.

The disperse dyes to be used which are only very sparingly soluble inwater and are mostly present in the dyeing liquor in the form of a finedispersion, can belong to a wide range of dye classes, for example theacridone, azo, anthraquinone, coumarin, methane, perinone,naphthoquinone-imine, quinophthalone, styryl or nitro dyes. It is alsopossible to use mixtures of disperse dyes in the practice of thisinvention.

The amount of dye to be added to the liquor will depend on the desireddepth of shade; suitable amounts range in general from 0.01 to 10.0% byweight, preferably, 0.02 to 5.0% by weight, based on the textilematerial used.

The application of the UVA according to the invention, optionally incombination with dyeing, may take place from an aqueous liquor by acontinuous or batch procedure.

In the case of continuous dyeineg procedures the dyeing liquors, whichin addition to the dyes may include further auxiliaries, are applied tothe piece material by means, for example, of pad-mangling, spraying orknit padding, and are developed using thermofix or HT steam processes.

In the case of the batch procedure (exhaust procedure) the liquor ratiocan be chosen within a wide range, for example from 1:1 to 1:100,preferably from 1:6 to 1:50. The temperature at which dyeing is carriedout is at least 50° C. and generally not more than 140° C. It ispreferably within the range from 80° C. to 135° C.

The application of the UVA according to the invention is advantageouslycarried out by the exhaust method using an aqueous liquor. The liquorratio is preferably from 1:3 to 1:50, especially from 1:5 to 1:30. Theliquor temperature during application is preferably from 70° C. to 140°C., especially from 80° C. to 135° C.

Linear polyester fibres are preferably treated by the high temperatureprocess in closed and pressure-resistant apparatus at temperatures>100°C., preferably between 110° C. and 135° C., and at atmospheric orsuperatmospheric pressures. Examples of suitable closed vessels are arecirculation apparatus, such as cheese or beam dyeing apparatus, winchbecks, jet or drim dyeing machines, muff dyeing apparatus, paddles orjiggers.

In addition to the compound of formula (1) and the dyes, the liquorsaccording to the invention can comprise further customary additives, forexample dyeing assistants, stabilisers, complexing agents, carriers,thickeners, dust-binding agents, anionic or non-ionic dispersants,wetting agents, separating agents, frost protection agents, antifoams,preservatives and bactericides.

The dye baths may additionally contain mineral acids, examples beingsulfuric acid or phosphoric acid, or, more expediently, organic acids,for example aliphatic carboxylic acids such as formic acid, acetic acid,oxalic acid, or citric acid, and/or salts, such as ammonium acetate,ammonium sulfate or sodium acetate. The purpose of the acids inparticular is to establish the pH of the liquors used in accordance withthe invention, which is preferably between 4 and 6, in particularbetween 4.5 and 5.5.

The dyeing liquor comprising the UVA according to the invention, the dyeand, where appropriate, further adjuvants is advantageously adjusted toa pH of from 4.5 to 5.5. The exhaust temperature is increased at a rateof 2° C./min from 30° C. to 135° C. and is held at that value for from15 to 90 min.

The dyeing liquor is then cooled to from 60 to 80° C. The fibre materialis washed with water and, if necessary, subjected to a clearingtreatment in an alkaline medium. Afterwards the dyed fibres are rinsedagain and dried.

The textile fibre material to be treated with the UVA according to theinvention may be in a variety of made-up forms, for example as loosematerial, piece goods such as knitted or woven fabrics or as a yarn on,for example, cheeses, warp beams etc. The latter can have packagedensities of 200 to 600 g/l, in particular 400 to 450 g/l.

The dyeings or printings obtained by application of the compounds offormula (1) are characterised by outstanding light fastness, inparticular hot light fastness properties, and are therefore especiallysuitable for fibres used in the automotive or swimwear sectors or inso-called “outdoor” articles.

The following Examples illustrate the invention.

I. SYNTHESIS EXAMPLES Example 1.1

Synthesis of the Compound

A mixture of salicylic acid (20.9 g), salicylamide (21.0 g),N,N′-dimethylformamide (0.5 ml) and xylene (70 ml) is heated to 110° C.,and then thionyl chloride (36.0 g) is added dropwise. The reactionmixture is stirred for 5 hours at 126° C. After completion of reaction,the reaction mixture is gradually cooled down at 10° C. and then stirredfor 1 hour. The precipitate is filtered and washed with methanol anddried under vacuum to yield 2-(2-hydroxyphenyl)-4H-1,3-benzoxazin-4-one(19.1 g).

30% sodium methylate in methanol (13.0 g) is added to the mixture ofmethanol (140 ml) and 4-pyridinecarboxamidine hydrochloride (7.5 g)which is prepared according to the patent of U.S. Pat. No. 6,004,965 atroom temperature. Then, 2-(2-hydroxyphenyl)-4H-1,3-benzoxazin-4-one(12.1 g) is added at 35° C. The reaction mixture is stirred for 4 hoursat 50° C. After cooling of the reaction mixture to room temperature, theprecipitate is collected by suction filtration, washed with methanol andwater and dried at 60° C. under vacuum to yield2,4-bis(2-hydroxyphenyl)-6-(4-pyridinyl)-1,3,5-triazine (8.9 g). Meltingpoint: 258-260° C. λ_(max)=280 nm/352 nm.

Example 1.2

Synthesis of the Compound

A mixture of salicylic acid (132 g), salicylamide (126 g),N,N′-dimethylformamide (3 ml) and xylene (240 ml) is heated to 110° C.,and then thionyl chloride (216 g) is added dropwise. The reactionmixture is stirred for 5 hours at 126° C. After completion of reaction,the reaction mixture is gradually cooled down at 10° C. and then stirredfor 1 hour. The precipitate is filtered and washed with methanol anddried under vacuum to yield 2-(2-hydroxyphenyl)-4H-1,3-benzoxazin-4-one(143 g).

30% sodium methylate in methanol (9.0 g) is added to the mixture ofmethanol (140 ml) and 2-pyrimidinecarboxamidine hydrochloride (7.9 g)which is prepared according to the patent of WO 2011/024056 A2 at roomtemperature. Then, 2-(2-hydroxyphenyl)-4H-1,3-benzoxazin-4-one (12.6 g)is added at 35° C. The reaction mixture is stirred for 4 hours at 50° C.After cooling of the reaction mixture to room temperature, theprecipitate is collected by suction filtration, washed with methanol andwater and dried at 60° C. under vacuum to yield2,4-bis(2-hydroxyphenyl)-6-(2-pyrimidinyl)-1,3,5-triazine (11.8 g).Melting point: 321-325° C. (decomposed). λ_(max)=280 nm/354 nm.

Examples 1.3-1.16

Analogously to the procedure described in Example 1.1, the compoundslisted in Table 1 are prepared.

TABLE 1 Compound R₁ R₂ R₃ V W X Y (105) H H H N CH CH CH (106) H CH₃ H NCH CH CH (107) H OCH₃ H N CH CH CH (108) H Cl H N CH CH CH (109) H Br HN CH CH CH (110) H H H CH CH CH N (111) H OH H CH CH CH N (112) H CH₃ HCH CH CH N (113) H OCH₃ H CH CH CH N (114) H Cl H CH CH CH N (115) H BrH CH CH CH N (116) H H H CH CH N CH (117) H CH₃ H CH CH N CH (118) HOCH₃ H CH CH N CH (119) H Cl H CH CH N CH (120) H Br H CH CH N CH (121)H H H CH N N CH (122) H CH₃ H CH N N CH (123) H OCH₃ H CH N N CH (124) HCl H CH N N CH (125) H Br H CH N N CH (126) H H CH₃ N CH CH CH (127) H HOCH₃ N CH CH CH (128) H H CN N CH CH CH (129) H H CF₃ N CH CH CH (130) HH Cl N CH CH CH (131) H H Br N CH CH CH (132) H H CH₃ CH CH CH N (133) HH OCH₃ CH CH CH N (134) H H CN CH CH CH N (135) H H CF₃ CH CH CH N (136)H H Cl CH CH CH N (137) H H Br CH CH CH N (138) H H CH₃ CH CH N CH (139)H H OCH₃ CH CH N CH (140) H H CN CH CH N CH (141) H H CF₃ CH CH N CH(142) H H Cl CH CH N CH (143) H H Br CH CH N CH (144) H H CH₃ CH N N CH(145) H H OCH₃ CH N N CH (146) H H CN CH N N CH (147) H H CF₃ CH N N CH(148) H H Cl CH N N CH (149) H H Br CH N N CH (150) H OH CH₃ N CH CH CH(151) H OH OCH₃ N CH CH CH (152) H OH CF₃ N CH CH CH (153) H OH Cl N CHCH CH (154) H OH Br N CH CH CH (155) H OH CH₃ CH CH CH N (156) H OH OCH₃CH CH CH N (157) H OH CF₃ CH CH CH N (158) H OH Cl CH CH CH N (159) H OHBr CH CH CH N (160) H OH CH₃ CH CH N CH (161) H OH OCH₃ CH CH N CH (162)H OH CF₃ CH CH N CH (163) H OH Cl CH CH N CH (164) H OH Br CH CH N CH(165) H OH CH₃ CH N N CH (166) H OH OCH₃ CH N N CH (167) H OH CF₃ CH N NCH (168) H OH Cl CH N N CH (169) H OH Br CH N N CH (170) CH₃ H H N CH CHCH (171) CH₃ H CH₃ N CH CH CH (172) CH₃ H OCH₃ N CH CH CH (173) CH₃ H CNN CH CH CH (174) CH₃ H CF₃ N CH CH CH (175) CH₃ H Cl N CH CH CH (176)CH₃ H Br N CH CH CH (177) CH₃ H H CH CH CH N (178) CH₃ H CH₃ CH CH CH N(179) CH₃ H OCH₃ CH CH CH N (180) CH₃ H CN CH CH CH N (181) CH₃ H CF₃ CHCH CH N (182) CH₃ H Cl CH CH CH N (183) CH₃ H Br CH CH CH N (184) CH₃ HH CH CH N CH (185) CH₃ H CH₃ CH CH N CH (186) CH₃ H OCH₃ CH CH N CH(187) CH₃ H CN CH CH N CH (188) CH₃ H CF₃ CH CH N CH (189) CH₃ H Cl CHCH N CH (190) CH₃ H Br CH CH N CH (191) CH₃ H H CH N N CH (192) CH₃ HCH₃ CH N N CH (193) CH₃ H OCH₃ CH N N CH (194) CH₃ H CN CH N N CH (195)CH₃ H CF₃ CH N N CH (196) CH₃ H Cl CH N N CH (197) CH₃ H Br CH N N CH(198) OCH₃ H H N CH CH CH (199) OCH₃ H CH₃ N CH CH CH (200) OCH₃ H OCH₃N CH CH CH (201) OCH₃ H CN N CH CH CH (202) OCH₃ H CF₃ N CH CH CH (203)OCH₃ H Cl N CH CH CH (204) OCH₃ H Br CH CH CH N (205) OCH₃ H H CH CH CHN (206) OCH₃ H CH₃ CH CH CH N (207) OCH₃ H OCH₃ CH CH CH N (208) OCH₃ HCN CH CH CH N (209) OCH₃ H CF₃ CH CH CH N (210) OCH₃ H Cl CH CH CH N(211) OCH₃ H Br CH CH CH N (212) OCH₃ H H CH CH N CH (213) OCH₃ H CH₃ CHCH N CH (214) OCH₃ H OCH₃ CH CH N CH (215) OCH₃ H CN CH CH N CH (216)OCH₃ H CF₃ CH CH N CH (217) OCH₃ H Cl CH CH N CH (218) OCH₃ H Br CH CH NCH (219) OCH₃ H H CH N N CH (220) OCH₃ H CH₃ CH N N CH (221) OCH₃ H OCH₃CH N N CH (222) OCH₃ H CN CH N N CH (223) OCH₃ H CF₃ CH N N CH (224)OCH₃ H Cl CH N N CH (225) OCH₃ H Br CH N N CH (226) CH₃ OH CH₃ N CH CHCH (227) CH₃ OH OCH₃ N CH CH CH (228) CH₃ OH CF₃ N CH CH CH (229) CH₃ OHCl N CH CH CH (230) CH₃ OH Br N CH CH CH (231) CH₃ OH CH₃ CH CH CH N(232) CH₃ OH OCH₃ CH CH CH N (233) CH₃ OH CF₃ CH CH CH N (234) CH₃ OH ClCH CH CH N (235) CH₃ OH Br CH CH CH N (236) CH₃ OH CH₃ CH CH N CH (237)CH₃ OH OCH₃ CH CH N CH (238) CH₃ OH CF₃ CH CH N CH (239) CH₃ OH Cl CH CHN CH (240) CH₃ OH Br CH CH N CH (241) CH₃ OH CH₃ CH N N CH (242) CH₃ OHOCH₃ CH N N CH (243) CH₃ OH CF₃ CH N N CH (244) CH₃ OH Cl CH N N CH(245) CH₃ OH Br CH N N CH (246) OCH₃ OH OCH₃ N CH CH CH (247) OCH₃ OHCF₃ N CH CH CH (248) OCH₃ OH Cl N CH CH CH (249) OCH₃ OH Br N CH CH CH(250) OCH₃ OH OCH₃ CH CH CH N (251) OCH₃ OH CF₃ CH CH CH N (252) OCH₃ OHCl CH CH CH N (253) OCH₃ OH Br CH CH CH N (254) OCH₃ OH CF₃ CH CH N CH(255) OCH₃ OH Cl CH CH N CH (256) OCH₃ OH Br CH CH N CH (257) OCH₃ OHOCH₃ CH N N CH (258) OCH₃ OH CF₃ CH N N CH (259) OCH₃ OH Cl CH N N CH(260) OCH₃ OH Br CH N N CH

II. APPLICATION EXAMPLES

II.1. Dyeing of Polyester

Specimens of 10 g of a PES knit-fabric (5-4212) are dyed by a laboratoryhigh temperature dyeing machine Labomat BFA-16 (Mathis) with a dyeingliquor containing

-   -   1.0 g/l ammonium sulphate,    -   0.5 g/l wetting agent,    -   1.0 g/l dispersing agent,

as well as the 0.218% by weight, based on the weight of the fabric, ofthe dyestuff Teratop® Yellow HL-G-01 150% (supplied by Huntsman), 0.112%by weight, based on the weight of the fabric, of the dyestuff Teratop®Red HL (supplied by Huntsman), and 0.142% by weight, based on the weightof the fabric, of the dyestuff Teratop® Blue HL-B 150% (supplied byHuntsman) and the compound of formula (103), (111) or (127),respectively, in the amounts given in Table 2 according to the exhaustmethod (liquor ratio 1:20, 60 min/135° C.). After cooling to about 80°C. the specimens are subjected to a reductive aftertreatment (20 min/75°C.) with a clearing liquor containing

-   -   2.0 g/l sodium hydrosulfite,    -   5.0 g/l 30% NaOH,    -   1.0 g/l soaping agent (Eriopon® OS, supplied by Huntsman) and        subsequently rinsed with water and dried.

The dyeings so obtained are tested for hot lightfastness according toDIN 75202 (FAKRA).

The results are summarised in Table 2.

The percentages in Table 2 are % by weight and relate to the weight ofthe fabric.

TABLE 2 Hot ligthfastness ratings* of grey dyeings obtained withdifferent amounts of UVA Amount UVA (103) (111) (127) 0% 2.5 2.5 2.5 2%3.1 3.1 3.3 4% 3.4 3.6 3.7 6% 3.6 3.6 3.8 *1 to 5 decimal ratingaccording to grey scale ISO 105-A02

II.2. Dyeing of Polyester

Specimens of 10 g of a PES knit-fabric (5-4212) are dyed by a laboratoryhigh temperature dyeing machine Labomat BFA-16 (Mathis) with a dyeingliquor containing

-   -   1.0 g/l ammonium sulphate,    -   0.5 g/l wetting agent,    -   1.0 g/l dispersing agent,

as well as the 0.20% by weight, based on the weight of the fabric, ofthe dyestuff Teratop® Yellow HL-G-01 150% (supplied by Huntsman), 0.11%by weight, based on the weight of the fabric, of the dyestuff Teratop®Red HL (supplied by Huntsman), and 0.26% by weight, based on the weightof the fabric, of the dyestuff Teratop® Blue HL-GR (supplied byHuntsman) and the compound of formula (110), (116), (121), (133) or(145), respectively, in the amounts given in Table 3 according to theexhaust method (liquor ratio 1:20, 60 min/135° C.).

After cooling to about 80° C. the specimens are subjected to a reductiveaftertreatment (20 min/75° C.) with a clearing liquor containing

-   -   2.0 g/l sodium hydrosulfite,    -   5.0 g/l 30% NaOH,    -   1.0 g/l soaping agent (Eriopon® OS, supplied by Huntsman)

and subsequently rinsed with water and dried.

The dyeings so obtained are tested for hot lightfastness according toDIN 75202 (FAKRA).

The results are summarised in Table 3.

The percentages in Table 3 are % by weight and relate to the weight ofthe fabric.

TABLE 3 Hot ligthfastness ratings* of grey dyeings obained withdifferent amounts of UVA Amount UVA (110) (116) (121) (133) (145) 0% 2.62.6 2.7 2.7 2.7 2% 3.5 3.8 3.6 3.8 3.8 4% 3.8 4.0 3.9 3.9 4.1 6% 3.9 4.13.9 4.2 4.1 *1 to 5 decimal rating according to grey scale ISO 105-A02

1. A compound of formula

wherein V, W, X and Y represent N or CH, at least one of V, W, X and Ybeing N and at least two of V, W, X and Y being CH; and R₁, R₂ and R₃are each independently of the other hydrogen, C₁-C₈alkyl, C₁-C₈alkoxy,nitro, cyano, trifluoromethyl, halogen or hydroxy; with the proviso thatthe compounds of formulae

are excluded.
 2. A The compound of formula (1) according to claim 1,wherein X is N and V, W and Y are CH.
 3. A The compound of formula (1)according to claim 1, wherein Y is N and V, W and X are CH.
 4. A Thecompound of formula (1) according to claim 1, wherein V is N and W, Xand Yare CH.
 5. A The compound of formula (1) according to claim 1,wherein X and W denote N and V and Y are CH.
 6. A The compound offormula (1) according to claim 1, wherein R₁ is hydrogen or methoxy. 7.A The compound of formula (1) according to claim 1, wherein R₂ ishydrogen or hydroxy.
 8. A The compound of formula (1) according to claim1, wherein R₃ is hydrogen or methoxy.
 9. The process for the preparationof a compound of formula (1) according to claim 1, which comprises (I).to prepare the 2-aryl-4H-1,3-benzoxazin-4-one (4) by acid-catalysed ringclosure reaction of the salicylamide derivative (2) with the carboxylicacid (3),

and (II). to react the thus obtained 2-aryl-4H-1,3-benzoxazin-4-one (4)with the amidine (5) to provide the triazine derivative of formula (1),

wherein R₁, R₂, R₃, X, Y, V and W are as defined in claim
 1. 10. Theprocess for the photochemical stabilisation of undyed, dyed or printedtextile fibre material, which comprises treating the textile fibrematerial with a liquor containing at least one compound of formula (1)according to claim
 1. 11. The process according to claim 10, wherein thetextile fibre material comprises polyester fibres.
 12. The process forthe photochemical stabilisation of dyed textile fibre material accordingto claim 10, wherein the compound of formula (1) is applied as a part ofthe dyeing liquor.
 13. (canceled)